title: Darzens reaction of acyl phosphonates with alpha-bromo ketones: selective synthesis of cis- and trans-epoxyphosphonates.
abstract: Acyl phosphonates with alpha-halo ketones in the presence of bases at room temperature afford cis- and trans-epoxyphosphonates in good chemical yields and high selectivities using different bases. The diastereoselectivity of this reaction is easily controlled by changing the base. Changing the base from Cs2CO3 to DBU changed the diastereomeric ratio (trans/cis) from 3/2 to 9/1. Moreover, the treatment of the trans isomer with DBU showed a complete conversion to the corresponding cis isomer.
authors.affiliation: Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey. asdemir@metu.edu.tr
authors.forename: Ayhan S
authors.initials: AS
authors.lastname: Demir
authors.forename: Mustafa
authors.initials: M
authors.lastname: Emrullahoglu
authors.forename: Eser
authors.initials: E
authors.lastname: Pirkin
authors.forename: Nazmiye
authors.initials: N
authors.lastname: Akca
mesh_terms: D000097:Acetonitriles / Q000737:chemistry; D001966:Bromine / Q000737:chemistry*; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000097:Acetonitriles; D004852:Epoxy Compounds; D007659:Ketones; D063065:Organophosphonates; D001966:Bromine; C032159:acetonitrile